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Tetrasubstituted benzenes
8217064 Tetrasubstituted benzenes
Patent Drawings:Drawing: 8217064-3    
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Inventor: Shapiro, et al.
Date Issued: July 10, 2012
Application: 12/341,201
Filed: December 22, 2008
Inventors: Shapiro; Gideon (Gainesville, FL)
Chesworth; Richard (Boston, MA)
Assignee: EnVivo Pharmaceuticals, Inc. (Watertown, MA)
Primary Examiner: Anderson; Rebecca
Assistant Examiner: Otton; Alicia L
Attorney Or Agent: Wilmer Cutler Pickering Hale and Dorr LLP
U.S. Class: 514/362; 514/364; 514/570; 548/126; 562/469
Field Of Search:
International Class: A61K 31/4245; A61K 31/192; C07D 498/00; A61K 31/433; C07C 59/48
U.S Patent Documents:
Foreign Patent Documents: 4239150; 19530204; 19530205; 184752; 260924; 405602; 415889; 254971; 434517; 275354; 382375; 405782; 759425; 757669; 802186; 716082; 1484304; 01604970; 01650183; 1764075; 1847524; 01849762; 01847524; 1255726; 01808432; 6978; 2473507; 2736053; 2830861; 2051043; 2065654; 2255092; 2253624; 7247235; 3598327; WO 95/01326; WO 95/29682; WO 96/22770; WO 97/01335; WO 97/01536; WO 97/27847; WO 97/27857; WO 97/28115; WO 97/28137; WO 97/28149; WO 98/00134; WO 98/31697; WO 99/63983; WO 00/05221; WO 00/31053; WO 01/36365; WO 01/58852; WO 01/87826; WO 02/13824; WO 02/074743; WO 02/081428; WO 03/042153; WO 03/074050; WO 2004/064771; WO 2004/065354; WO-2004074232; WO 2004/087159; WO 2004/096747; WO 2004/096781; WO 2004/110350; WO 2005/000309; WO 2005/037763; WO 2005/054213; WO-2005054193; WO 2005/065683; WO 2005/094810; WO 2005/097759; WO 2005/097775; WO 2005/108362; WO 2005/110963; WO 2005/115990; WO 2006/004030; WO 2006/008558; WO 2006/021441; WO 2006/025783; WO 2006/043064; WO 2006/044732; WO-2006041874; WO-2006043064; WO 2006/045554; WO 2006/046575; WO 2006/048219; WO 2006/123165; WO 2007/039736; WO 2007/056366; WO 2007/056497; WO 2007/058304; WO 2007/058305; WO 2007/075895; WO 2007/102580; WO 2007/110667; WO 2007/116228; WO 2007/124394; WO 2007/125364; WO 2007/140174; WO 2007/140183; WO 2008/013213; WO 2008/039882; WO 2008/108378; WO 2008/137102
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Abstract: Tetrasubstituted benzenes that act as modulators of gamma secretase and their use in the treatment of one or more symptoms of treating neurodegenerative disorders, e.g., Alzheimer's disease, are described.
Claim: What is claimed is:

1. A compound selected from: (R)-2-(5-chloro-6-(2,2,2-trifluoroethoxy)-4'-(trifluoromethyl)biphenyl-3-- yl)-3-cyclobutylpropanoic acid; (S)-2-(5-chloro-6-(2,2,2-trifluoroethoxy)-4'-(trifluoromethyl)biphenyl-3-- yl)-3-cyclobutylpropanoic acid; (R)-2-(5-chloro-6-(2,2,2-trifluoroethoxy)-4'-(trifluoromethyl)biphenyl-3-- yl)-2-cyclopentylacetic acid; (S)-2-(5-chloro-6-(2,2,2-trifluoroethoxy)-4'-(trifluoromethyl)biphenyl-3-- yl)-2-cyclopentylacetic acid; (R)-2-(5-chloro-6-(2,2,2-trifluoroethoxy)-4'-(trifluoromethyl)biphenyl-3-- yl)-3-cyclopropylpropanoic acid; (S)-2-(5-chloro-6-(2,2,2-trifluoroethoxy)-4'-(trifluoromethyl)biphenyl-3-- yl)-3-cyclopropylpropanoic acid; (R)-2-(5-chloro-6-(2,2,2-trifluoroethoxy)-4'-(trifluoromethyl)biphenyl-3-- yl)-4-methylpentanoic acid; (S)-2-(5-chloro-6-(2,2,2-trifluoroethoxy)-4'-(trifluoromethyl)biphenyl-3-- yl)-4-methylpentanoic acid; (R)-4-methyl-2-(6-(2,2,2-trifluoroethoxy)-4',5-bis(trifluoromethyl)biphen- yl-3-yl)pentanoic acid; (S)-4-methyl-2-(6-(2,2,2-trifluoroethoxy)-4',5-bis(trifluoromethyl)biphen- yl-3-yl)pentanoic acid; (R)-3-cyclopropyl-2-(6-(2,2,2-trifluoroethoxy)-4',5-bis(trifluoromethyl)b- iphenyl-3-yl)propanoic acid; (S)-3-cyclopropyl-2-(6-(2,2,2-trifluoroethoxy)-4',5-bis(trifluoromethyl)b- iphenyl-3-yl)propanoic acid; (R)-2-(5-chloro-4'-(methylthio)-6-(2,2,2-trifluoroethoxy)biphenyl-3-yl)-2- -cyclopentylacetic acid; (S)-2-(5-chloro-4'-(methylthio)-6-(2,2,2-trifluoroethoxy)biphenyl-3-yl)-2- -cyclopentylacetic acid; (R)-2-(5-chloro-4'-(methylthio)-6-(2,2,2-trifluoroethoxy)biphenyl-3-yl)-3- -cyclobutylpropanoic acid; (S)-2-(5-chloro-4'-(methylthio)-6-(2,2,2-trifluoroethoxy)biphenyl-3-yl)-3- -cyclobutylpropanoic acid; (R)-2-(5-chloro-4'-(methylthio)-6-(2,2,2-trifluoroethoxy)biphenyl-3-yl)-3- -cyclopropylpropanoic acid; (S)-2-(5-chloro-4'-(methylthio)-6-(2,2,2-trifluoroethoxy)biphenyl-3-yl)-3- -cyclopropylpropanoic acid; (R)-2-(5-chloro-4'-(methylthio)-6-(2,2,2-trifluoroethoxy)biphenyl-3-yl)-4- -methylpentanoic acid; (S)-2-(5-chloro-4'-(methylthio)-6-(2,2,2-trifluoroethoxy)biphenyl-3-yl)-4- -methylpentanoic acid; (R)-2-(5-chloro-4'-isopropyl-6-(2,2,2-trifluoroethoxy)biphenyl-3-yl)-2-cy- clopentylacetic acid; (S)-2-(5-chloro-4'-isopropyl-6-(2,2,2-trifluoroethoxy)biphenyl-3-yl)-2-cy- clopentylacetic acid; (R)-2-(5-chloro-4'-isopropyl-6-(2,2,2-trifluoroethoxy)biphenyl-3-yl)-3-cy- clobutylpropanoic acid; (S)-2-(5-chloro-4'-isopropyl-6-(2,2,2-trifluoroethoxy)biphenyl-3-yl)-3-cy- clobutylpropanoic acid; (R)-2-(5-chloro-4'-isopropyl-6-(2,2,2-trifluoroethoxy)biphenyl-3-yl)-3-cy- clopropylpropanoic acid; (S)-2-(5-chloro-4'-isopropyl-6-(2,2,2-trifluoroethoxy)biphenyl-3-yl)-3-cy- clopropylpropanoic acid; (R)-2-(5-chloro-4'-isopropyl-6-(2,2,2-trifluoroethoxy)biphenyl-3-yl)-4-me- thylpentanoic acid; (S)-2-(5-chloro-4'-isopropyl-6-(2,2,2-trifluoroethoxy)biphenyl-3-yl)-4-me- thylpentanoic acid; (R)-2-(3-(benzo[c][1,2,5]oxadiazol-5-yl)-4-(2,2,2-trifluoroethoxy)-5-(tri- fluoromethyl)phenyl)-4-methylpentanoic acid; (S)-2-(3-(benzo[c][1,2,5]oxadiazol-5-yl)-4-(2,2,2-trifluoroethoxy)-5-(tri- fluoromethyl)phenyl)-4-methylpentanoic acid; (R)-2-(3-(benzo[c][1,2,5]oxadiazol-5-yl)-4-(2,2,2-trifluoroethoxy)-5-(tri- fluoromethyl)phenyl)-3-cyclopropylpropanoic acid; (S)-2-(3-(benzo[c][1,2,5]oxadiazol-5-yl)-4-(2,2,2-trifluoroethoxy)-5-(tri- fluoromethyl)phenyl)-3-cyclopropylpropanoic acid; (R)-2-(3-(benzo[c][1,2,5]thiadiazol-5-yl)-4-(2,2,2-trifluoroethoxy)-5-(tr- ifluoromethyl)phenyl)-3-cyclopropylpropanoic acid; (S)-2-(3-(benzo[c][1,2,5]thiadiazol-5-yl)-4-(2,2,2-trifluoroethoxy)-5-(tr- ifluoromethyl)phenyl)-3-cyclopropylpropanoic acid; (R)-2-(3-(benzo[c][1,2,5]thiadiazol-5-yl)-4-(2,2,2-trifluoroethoxy)-5-(tr- ifluoromethyl)phenyl)-4-methylpentanoic acid; or(S)-2-(3-(benzo[c][1,2,5]thiadiazol-5-yl)-4-(2,2,2-trifluoroethoxy)-5-(tr- ifluoromethyl)phenyl)-4-methylpentanoic acid; or a pharmaceutically acceptable salt thereof.

2. The compound of claim 1 selected from: (R)-2-(5-chloro-6-(2,2,2-trifluoroethoxy)-4'-(trifluoromethyl)biphenyl-3-- yl)-3-cyclobutylpropanoic acid; (S)-2-(5-chloro-6-(2,2,2-trifluoroethoxy)-4'-(trifluoromethyl)biphenyl-3--yl)-3-cyclobutylpropanoic acid; (R)-2-(5-chloro-6-(2,2,2-trifluoroethoxy)-4'-(trifluoromethyl)biphenyl-3-- yl)-2-cyclopentylacetic acid; (S)-2-(5-chloro-6-(2,2,2-trifluoroethoxy)-4'-(trifluoromethyl)biphenyl-3-- yl)-2-cyclopentylacetic acid; (R)-2-(5-chloro-6-(2,2,2-trifluoroethoxy)-4'-(trifluoromethyl)biphenyl-3-- yl)-3-cyclopropylpropanoic acid; (S)-2-(5-chloro-6-(2,2,2-trifluoroethoxy)-4'-(trifluoromethyl)biphenyl-3-- yl)-3-cyclopropylpropanoic acid; (R)-2-(5-chloro-6-(2,2,2-trifluoroethoxy)-4'-(trifluoromethyl)biphenyl-3-- yl)-4-methylpentanoic acid; or (S)-2-(5-chloro-6-(2,2,2-trifluoroethoxy)-4'-trifluoromethyl)biphenyl-3-y- l)-4-methylpentanoic acid; or a pharmaceutically acceptable saltthereof.

3. The compound or a pharmaceutically acceptable salt of (R)-2-(5-chloro-6-(2,2,2-trifluoroethoxy)-4'-(trifluoromethyl)biphenyl-3-- yl)-3-cyclobutylpropanoic acid.

4. The compound or a pharmaceutically acceptable salt of (S)-2-(5-chloro-6-(2,2,2-trifluoroethoxy)-4'-(trifluoromethyl)biphenyl-3-- yl)-3-cyclobutylpropanoic acid.

5. A pharmaceutical composition comprising: a compound selected from: (R)-2-(5-chloro-6-(2,2,2-trifluoroethoxy)-4'-(trifluoromethyl)biphenyl-3-- yl)-3-cyclobutylpropanoic acid; (S)-2-(5-chloro-6-(2,2,2-trifluoroethoxy)-4'-(trifluoromethyl)biphenyl-3-- yl)-3-cyclobutylpropanoic acid; (R)-2-(5-chloro-6-(2,2,2-trifluoroethoxy)-4'-(trifluoromethyl)biphenyl-3-- yl)-2-cyclopentylacetic acid; (S)-2-(5-chloro-6-(2,2,2-trifluoroethoxy)-4'-(trifluoromethyl)biphenyl-3-- yl)-2-cyclopentylacetic acid; (R)-2-(5-chloro-6-(2,2,2-trifluoroethoxy)-4'-(trifluoromethyl)biphenyl-3-- yl)-3-cyclopropylpropanoic acid; (S)-2-(5-chloro-6-(2,2,2-trifluoroethoxy)-4'-(trifluoromethyl)biphenyl-3-- yl)-3-cyclopropylpropanoic acid; (R)-2-(5-chloro-6-(2,2,2-trifluoroethoxy)-4'-(trifluoromethyl)biphenyl-3-- yl)-4-methylpentanoic acid; (S)-2-(5-chloro-6-(2,2,2-trifluoroethoxy)-4'-(trifluoromethyl)biphenyl-3-- yl)-4-methylpentanoic acid; (R)-4-methyl-2-(6-(2,2,2-trifluoroethoxy)-4',5-bis(trifluoromethyl)biphen- yl-3-yl)pentanoic acid; (S)-4-methyl-2-(6-(2,2,2-trifluoroethoxy)-4',5-bis(trifluoromethyl)biphen- yl-3-yl)pentanoic acid; (R)-3-cyclopropyl-2-(6-(2,2,2-trifluoroethoxy)-4',5-bis(trifluoromethyl)b- iphenyl-3-yl)propanoic acid; (S)-3-cyclopropyl-2-(6-(2,2,2-trifluoroethoxy)-4',5-bis(trifluoromethyl)b- iphenyl-3-yl)propanoic acid; (R)-2-(5-chloro-4'-(methylthio)-6-(2,2,2-trifluoroethoxy)biphenyl-3-yl)-2- -cyclopentylacetic acid; (S)-2-(5-chloro-4'-(methylthio)-6-(2,2,2-trifluoroethoxy)biphenyl-3-yl)-2- -cyclopentylacetic acid; (R)-2-(5-chloro-4'-(methylthio)-6-(2,2,2-trifluoroethoxy)biphenyl-3-yl)-3- -cyclobutylpropanoic acid; (S)-2-(5-chloro-4'-(methylthio)-6-(2,2,2-trifluoroethoxy)biphenyl-3-yl)-3- -cyclobutylpropanoic acid; (R)-2-(5-chloro-4'-(methylthio)-6-(2,2,2-trifluoroethoxy)biphenyl-3-yl)-3- -cyclopropylpropanoic acid; (S)-2-(5-chloro-4'-(methylthio)-6-(2,2,2-trifluoroethoxy)biphenyl-3-yl)-3- -cyclopropylpropanoic acid; (R)-2-(5-chloro-4'-(methylthio)-6-(2,2,2-trifluoroethoxy)biphenyl-3-yl)-4- -methylpentanoic acid; (S)-2-(5-chloro-4'-(methylthio)-6-(2,2,2-trifluoroethoxy)biphenyl-3-yl)-4- -methylpentanoic acid; (R)-2-(5-chloro-4'-isopropyl-6-(2,2,2-trifluoroethoxy)biphenyl-3-yl)-2-cy- clopentylacetic acid; (S)-2-(5-chloro-4'-isopropyl-6-(2,2,2-trifluoroethoxy)biphenyl-3-yl)-2-cy- clopentylacetic acid; (R)-2-(5-chloro-4'-isopropyl-6-(2,2,2-trifluoroethoxy)biphenyl-3-yl)-3-cy- clobutylpropanoic acid; (S)-2-(5-chloro-4'-isopropyl-6-(2,2,2-trifluoroethoxy)biphenyl-3-yl)-3-cy- clobutylpropanoic acid; (R)-2-(5-chloro-4'-isopropyl-6-(2,2,2-trifluoroethoxy)biphenyl-3-yl)-3-cy- clopropylpropanoic acid; (S)-2-(5-chloro-4'-isopropyl-6-(2,2,2-trifluoroethoxy)biphenyl-3-yl)-3-cy- clopropylpropanoic acid; (R)-2-(5-chloro-4'-isopropyl-6-(2,2,2-trifluoroethoxy)biphenyl-3-yl)-4-me- thylpentanoic acid; (S)-2-(5-chloro-4'-isopropyl-6-(2,2,2-trifluoroethoxy)biphenyl-3-yl)-4-me- thylpentanoic acid; (R)-2-(3-(benzo[c][1,2,5]oxadiazol-5-yl)-4-(2,2,2-trifluoroethoxy)-5-(tri- fluoromethyl)phenyl)-4-methylpentanoic acid; (S)-2-(3-(benzo[c][1,2,5]oxadiazol-5-yl)-4-(2,2,2-trifluoroethoxy)-5-(tri- fluoromethyl)phenyl)-4-methylpentanoic; (R)-2-(3-(benzo[c][1,2,5]oxadiazol-5-yl)-4-(2,2,2-trifluoroethoxy)-5-(tri- fluoromethyl)phenyl)-3-cyclopropylpropanoic acid; (S)-2-(3-(benzo[c][1,2,5]oxadiazol-5-yl)-4-(2,2,2-trifluoroethoxy)-5-(tri- fluoromethyl)phenyl)-3-cyclopropylpropanoic acid; (R)-2-(3-(benzo[c][1,2,5]thiadiazol-5-yl)-4-(2,2,2-trifluoroethoxy)-5-(tr- ifluoromethyl)phenyl)-3-cyclopropylpropanoic acid; (S)-2-(3-(benzo[c][1,2,5]thiadiazol-5-yl)-4-(2,2,2-trifluoroethoxy)-5-(tr- ifluoromethyl)phenyl)-3-cyclopropylpropanoic acid; (R)-2-(3-(benzo[c][1,2,5]thiadiazol-5-yl)-4-(2,2,2-trifluoroethoxy)-5-(tr- ifluoromethyl)phenyl)-4-methylpentanoic acid; or(S)-2-(3-(benzo[c][1,2,5]thiadiazol-5-yl)-4-(2,2,2-trifluoroethoxy)-5-(tr- ifluoromethyl)phenyl)-4-methylpentanoic acid or a pharmaceutically acceptable salt thereof and a pharmaceutically acceptable excipient, carrier or diluent.

6. The pharmaceutical composition of claim 5 in solid dosage form.

7. The pharmaceutical composition of claim 5 in oral dosage form.

8. The pharmaceutical composition of claim 7, wherein said oral dosage form is in the form of a tablet, pill, dragee, lozenge or capsule.

9. The pharmaceutical composition of claim 7, wherein said oral dosage form is in the form of a tablet or capsule.

10. A pharmaceutical composition comprising: a compound selected from: (R)-2-(5-chloro-6-(2,2,2-trifluoroethoxy)-4'-(trifluoromethyl)biphenyl-3-- yl)-3-cyclobutylpropanoic acid; (S)-2-(5-chloro-6-(2,2,2-trifluoroethoxy)-4'-(trifluoromethyl)biphenyl-3-- yl)-3-cyclobutylpropanoic acid; (R)-2-(5-chloro-6-(2,2,2-trifluoroethoxy)-4'-(trifluoromethyl)biphenyl-3-- yl)-2-cyclopentylacetic acid; (S)-2-(5-chloro-6-(2,2,2-trifluoroethoxy)-4'-(trifluoromethyl)biphenyl-3-- yl)-2-cyclopentylacetic acid; (R)-2-(5-chloro-6-(2,2,2-trifluoroethoxy)-4'-(trifluoromethyl)biphenyl-3-- yl)-3-cyclopropylpropanoic acid; (S)-2-(5-chloro-6-(2,2,2-trifluoroethoxy)-4'-(trifluoromethyl)biphenyl-3-- yl)-3-cyclopropylpropanoic acid; (R)-2-(5-chloro-6-(2,2,2-trifluoroethoxy)-4'-(trifluoromethyl)biphenyl-3-- yl)-4-methylpentanoic acid; or(S)-2-(5-chloro-6-(2,2,2-trifluoroethoxy)-4'-(trifluoromethyl)biphenyl-3-- yl)-4-methylpentanoic acid or a pharmaceutically acceptable salt thereof and a pharmaceutically acceptable excipient, carrier or diluent.

11. The pharmaceutical composition of claim 10 in solid dosage form.

12. The pharmaceutical composition of claim 10 in oral dosage form.

13. The pharmaceutical composition of claim 12, wherein said oral dosage form is in the form of a tablet, pill, dragee, lozenge or capsule.

14. The pharmaceutical composition of claim 12, wherein said oral dosage form is in the form of a tablet or capsule.

15. A pharmaceutical composition comprising (R)-2-(5-chloro-6-(2,2,2-trifluoroethoxy)-4'-(trifluoromethyl)biphenyl-3-- yl)-3-cyclobutylpropanoic acid or a pharmaceutically acceptable salt thereof and a pharmaceutically acceptable excipient,carrier or diluent.

16. The pharmaceutical composition of claim 15 in solid dosage form.

17. The pharmaceutical composition of claim 15 in oral dosage form.

18. The pharmaceutical composition of claim 17, wherein said oral dosage form is in the form of a tablet, pill, dragee, lozenge or capsule.

19. The pharmaceutical composition of claim 17, wherein said oral dosage form is in the form of a tablet or capsule.

20. A pharmaceutical composition comprising (S)-2-(5-chloro-6-(2,2,2-trifluoroethoxy)-4'-(trifluoromethyl)biphenyl-3-- yl)-3-cyclobutylpropanoic acid or a pharmaceutically acceptable salt thereof and a pharmaceutically acceptable excipient,carrier or diluent.

21. The pharmaceutical composition of claim 20 in solid dosage form.

22. The pharmaceutical composition of claim 20 in oral dosage form.

23. The pharmaceutical composition of claim 22, wherein said oral dosage form is in the form of a tablet, pill, dragee, lozenge or capsule.

24. The pharmaceutical composition of claim 22, wherein said oral dosage form is in the form of a tablet or capsule.
Description:
 
 
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